Lithium hydroxide, monohydrate → 4-oxo-2-[(1-phenylcyclohexyl)methyl]-5-phenylmethoxy-1H-pyrimidine-6-carboxylic acid

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (255) (2.5 g, 5.27 mmol) in tetrahydrofuran (60.0 mL) was added a aqueous solution (30.0 mL) of LiOH.H2O (2.21 g, 52.67 mmol) and the reaction mixture was refluxed for 16 h. After completion of the reaction, the organic solvent was removed on a rotary evaporator and water (10.0 mL) was added. The aqueous solution was acidified with concentrated HCl to pH=5.0 at 0° C. to give a white solid which was filtered off. The solid residue was triturated in diethyl ether and filtered. After drying, 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid (256) was obtained (1.6 g, 72.58%) as a white solid.

Provenance & Evidence